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$63+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
ene. 15 — ene. 221
jue. 1/15
jue. 1/22
1 adult, Economy
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Cheap flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 16, 2025.

This United Airlines deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/315:40 amSDF - ORD
Nonstop1h 44mUnited Airlines
mar. 1/610:45 amORD - SDF
Nonstop1h 39mUnited Airlines
Deal found 12/13$173
This United Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/315:40 amSDF - ORD
Nonstop1h 44mUnited Airlines
jue. 1/15:54 pmORD - SDF
Nonstop1h 38mUnited Airlines
Deal found 12/14$175
This Southwest deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/258:10 amBNA - MDW
Nonstop1h 45mSouthwest
mié. 1/286:00 amMDW - BNA
Nonstop1h 35mSouthwest
Deal found 12/14$193
This United Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/259:50 amBNA - ORD
Nonstop2h 04mUnited Airlines
mié. 1/287:40 amORD - BNA
Nonstop1h 50mUnited Airlines
Deal found 12/14$193
This Southwest deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/2510:20 amBNA - ORD
Nonstop1h 55mSouthwest
mié. 1/282:15 pmORD - BNA
1 stop6h 40mSouthwest
Deal found 12/14$203
This United Airlines deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/312:19 pmCVG - ORD
Nonstop1h 36mUnited Airlines
jue. 1/17:10 amORD - CVG
Nonstop1h 29mUnited Airlines
Deal found 12/13$211
This American Airlines deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/318:05 amSDF - ORD
Nonstop1h 40mAmerican Airlines
mar. 1/610:10 amORD - SDF
1 stop7h 20mAmerican Airlines
Deal found 12/13$213
This Delta deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/251:00 pmBNA - ORD
1 stop6h 38mDelta
mié. 1/285:30 amORD - BNA
1 stop4h 29mDelta
Deal found 12/14$213
This Frontier deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/232:50 pmCVG - ORD
1 stop8h 34mFrontier
jue. 12/2512:39 pmORD - CVG
1 stop5h 39mFrontier
Deal found 12/16$213
This American Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/318:00 amSDF - ORD
1 stop7h 12mAmerican Airlines
jue. 1/18:53 pmORD - SDF
Nonstop1h 37mAmerican Airlines
Deal found 12/14$215
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/248:04 amLEX - ORD
Nonstop1h 40mAmerican Airlines
mié. 12/318:37 pmORD - LEX
Nonstop1h 35mAmerican Airlines
Deal found 12/16$217
This United Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/306:00 amLEX - ORD
Nonstop1h 55mUnited Airlines
sáb. 1/36:20 pmORD - LEX
Nonstop1h 44mUnited Airlines
Deal found 12/15$219

Find flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated diciembre 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$133
(United Airlines)

One-way from

$63
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$270

Good round-trip deal

$100 or less

Good one-way deal

$44 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
Search Deals
From Kentucky to Chicago (CHI)
Search Deals
One-way flight from Kentucky to Chicago (CHI)
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Kentucky to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 16, 2025.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Kentucky

Fly to

Chicago

Route

Depart

Return

Price

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

mar. 1/13

11:54 am-5:52 pm

1 stop6h 58m

Chicago O'Hare Intl

mar. 1/20

2:53 pm-10:20 pm

2 stops30h 27m

$158

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

sáb. 1/17

11:10 am-11:53 am

Nonstop1h 43m

Chicago O'Hare Intl

lun. 1/19

7:52 pm-10:30 pm

Nonstop1h 38m

$171

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

jue. 1/8

6:45 am-7:10 am

Nonstop1h 25m

Chicago Midway

lun. 1/12

10:00 am-12:15 pm

Nonstop1h 15m

$171

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

jue. 1/15

6:25 am-6:55 am

Nonstop1h 30m

Chicago Midway

jue. 1/22

7:55 pm-10:10 pm

Nonstop1h 15m

$171

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

jue. 2/5

8:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

lun. 2/9

7:50 pm-9:42 pm

Nonstop1h 52m

$171

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

jue. 1/15

8:46 am-9:12 am

2 stops25h 26m

Chicago O'Hare Intl

jue. 1/22

12:44 pm-11:26 pm

1 stop9h 42m

$171

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

mié. 1/14

11:45 am-1:20 pm

Nonstop1h 35m

Chicago Midway

lun. 1/26

6:00 am-7:35 am

Nonstop1h 35m

$171

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

mar. 1/20

8:30 pm-10:05 pm

Nonstop1h 35m

Chicago Midway

jue. 1/22

10:05 am-11:40 am

Nonstop1h 35m

$171

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

jue. 1/8

8:30 pm-10:05 pm

Nonstop1h 35m

Chicago Midway

sáb. 1/10

2:40 pm-4:10 pm

Nonstop1h 30m

$171

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

sáb. 1/17

5:45 am-7:30 am

Nonstop1h 45m

Chicago Midway

lun. 1/19

5:25 am-7:00 am

Nonstop1h 35m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

What is the cheapest month to book a flight from Kentucky to Chicago?

Currently, September is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $77). Flying from Kentucky to Chicago in July is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 16, 2025.

One of the essential ways to save on airfare from Kentucky to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 29% on airfare.

What is the cheapest day to fly from Kentucky to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kentucky to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kentucky to Chicago?

    There are many flights that can get you from Kentucky to Chicago in 1h 25m. Fly via United Airlines, Southwest, or Delta to get the fastest option. The distance from Kentucky to Chicago is about 271 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Kentucky to Chicago one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $38. American Airlines flights start at $48 while deals on United Airlines start at $54 one-way.

  • What are the most popular routes from Kentucky to Chicago?

    The most popular flight routes from Kentucky to Chicago are Nashville Intl - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl and Louisville Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Kentucky to Chicago?

    Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Iberia (84%), Copa Airlines (84%), Envoy Air( 83%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $686 for a flight from Kentucky to Chicago. The cheapest flight overall is $119 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $145.

  • Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

    Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.

  • Can I find deals for business class flights from Kentucky to Chicago?

    Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kentucky to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $77). Flying from Kentucky to Chicago in July is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Kentucky to Chicago

Discover the top 4 airlines that operate flights from Kentucky to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$275FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$260FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$114Average$275FlexibilityNo cancel feeOn-time69%
ContourCheapest$116Average$154FlexibilityNo cancel feeOn-timeN/A

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